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JOURNALS // Uspekhi Khimii // Archive

Usp. Khim., 2024 Volume 93, Issue 10, Pages 1–15 (Mi rcr4480)

This article is cited in 1 paper

Reaction of acetylenic carbanions with C=N bond: dynamics of development, synthetic divergence, environmental safety

E. Yu. Schmidt, B. A. Trofimov

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation

Abstract: This review highlights dynamics of development and synthetic application of the recently discovered reaction of acetylenic carbanions, generated in superbase media, with C=N bond of different classes of substrates. A fundamental feature of this reaction is its synthetic divergence, i.e. its ability to proceed in various directions that manifests in novel transformations to selectively deliver (depending on structure of the acetylenes and substrates with C=N bond) structurally different synthetically important products. The review also discusses cascade processes, in which the key intermediates containing the C=N bond add acetylenes thereby participating in the self-organization of diverse and potentially useful compounds. The competitive advantage of the reaction and its daughter branches is environmental safety (neutrality), based on the fundamental chemical nature of these reactions as addition processes that occur without the release of by-products.
The bibliography includes 133 references.

Keywords: acetylenes; imines; amines, propargylamines, superbases.

Received: 25.07.2024

DOI: 10.59761/RCR5145


 English version:
Russian Chemical Reviews, 2024, 93:10, 1–15

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© Steklov Math. Inst. of RAS, 2025